4-{[5-amino-1-({1-[(1-carboxyethyl)carbamoyl]ethyl}carbamoyl)pentyl]carbamoyl}-2-(2-aminopropanamido)butanoic acid

• ChemBase ID: 155462
• Molecular Formular: C20H36N6O8
• Molecular Mass: 488.53524
• Monoisotopic Mass: 488.25946214
• SMILES: CC(C(=O)NC(CCC(=O)NC(CCCCN)C(=O)NC(C)C(=O)NC(C)C(=O)O)C(=O)O)N
• Canonical SMILES: NCCCCC(C(=O)NC(C(=O)NC(C(=O)O)C)C)NC(=O)CCC(C(=O)O)NC(=O)C(N)C
• InChI: InChI=1S/C20H36N6O8/c1-10(22)16(28)26-14(20(33)34)7-8-15(27)25-13(6-4-5-9-21)18(30)23-11(2)17(29)24-12(3)19(31)32/h10-14H,4-9,21-22H2,1-3H3,(H,23,30)(H,24,29)(H,25,27)(H,26,28)(H,31,32)(H,33,34)
• InChIKey: MCIBYIIODNXVSL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[5-amino-1-({1-[(1-carboxyethyl)carbamoyl]ethyl}carbamoyl)pentyl]carbamoyl}-2-(2-aminopropanamido)butanoic acid
• IUPAC Traditional name: 4-{[5-amino-1-({1-[(1-carboxyethyl)carbamoyl]ethyl}carbamoyl)pentyl]carbamoyl}-2-(2-aminopropanamido)butanoic acid
• Synonyms: Peptidoglycan pentapeptide; Ala-D-γ-Glu-Lys-D-Ala-D-Ala

Database IDs

• CAS Number: 2614-55-3
• MDL Number: MFCD00133044
• PubChem SID: 162249600; 24890467
• PubChem CID: 4294676

CALCULATED PROPERTIES

• Acid pKa: 3.0360136
• H Acceptors: 10
• H Donor: 8
• LogD (pH = 5.5): -7.7390556
• LogD (pH = 7.4): -7.774335
• Log P: -7.7368436
• Molar Refractivity: 117.7895 cm^3
• Polarizability: 46.745827 Å^3
• Polar Surface Area: 243.04 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C20H36N6O8

DETAILS

Sigma Aldrich - A0910

Amino Acid Sequence
Ala-Glu-Lys-Ala-Ala
Application
Ala-D-γ-Glu-Lys-D-Ala-D-Ala is the pentapeptide tail of the peptidoglycan precursor UDPMurNAc-l-Ala-γ-d-Glu-l-Lys(Gly)(5)-d-Ala-d-Ala. Ala-D-γ-Glu-Lys-D-Ala-D-Ala is used to study the role of this peptide stem in peptidoglycan biosynthesis, degradation and function.
Biochem/physiol Actions
L-Ala-D-Glu-gamma-L-Lys-D-Ala-D-Ala, peptidoglycan pentapeptide, is the antigenic peptide determinant of peptidoglycan useful in studies of mechanisms of action of glycopeptide antibiotics.